Analysis of the pentafluorobenzoyl derivative of phenylethylamine utilizing negative ion chemical ionization and gas chromatography/mass spectrometry

Gashkoff, P.; Matalon, Reuben; Papa, Vincent M.; Sebasta, Dana

doi:10.1002/bms.1200160163

Cited by 4 publications

(2 citation statements)

References 6 publications

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“…As already mentioned above, primary and secondary amines yield PFBz derivatives with excellent REC response and are thus also frequently used for their GC-NICI-MS determination, as reported for amphetamine [41], memantine and amantadine [42], and rimantadine [55]. The phenylethylamine levels excreted by normal subjects and patients with phenylketonuria [56] and in human plasma [57] were measured by GC-NICI-MS using this derivative. Furthermore, this was applied to the trace level analysis of tobacco-specific nitrosamine-DNA adducts in smokers and non-smokers [58], and during an isotope tracer study on cholesterol metabolism with a detection limit of one fmol [59].…”

Section: Nici-gc-ms Of Pentafluorobenzoyl Derivativesmentioning

confidence: 99%

Electron-Capture Mass Spectrometry: A Powerful Tool in Biomedical Trace Level Analysis

Leis¹,

Fauler²,

Rechberger³

et al. 2004

CMC

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This review focuses on the advances in electron capture mass spectrometry. Electron-capture (EC) is a sensitive ionisation technique for mass spectrometry providing selectivity towards electrophoric compounds. Recent advances in instrumentation have led to a more widespread application of this method in biomedical and pharmaceutical analysis. After a brief introduction to EC-mass spectrometry (MS), potential targets for EC-MS analysis are defined and enhancement of sensitivity by electrophoric derivatisation is discussed. A wide range of applications is selected, including prostanoid analysis in biomedical systems (with the oxidative stress indicators isoprostanes) and the trace level analysis of endogenous low-molecular weight compounds. Application to the trace level gas chromatography-negative ion chemical ionization MS (GC-NICI-MS) analysis of complex glucuronides is also demonstrated, as well as a wide range of drugs analysed in human blood. The review should point out the versatility and unique sensitivity of the technique, making it useful for basic research in medicinal chemistry, as well as clinical diagnosis, pharmaceutical and toxicological applications.

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Section: Nici-gc-ms Of Pentafluorobenzoyl Derivativesmentioning

confidence: 99%

Electron-Capture Mass Spectrometry: A Powerful Tool in Biomedical Trace Level Analysis

Leis¹,

Fauler²,

Rechberger³

et al. 2004

CMC

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“…However, reactions which impart a halogenated moiety, such as the pentafluorobenzoyl derivatives (PFBoyl), offer the capability of enhanced GC/MS detection of hydroxyl-containing compounds when coupled with negative ion chemical ionization (NICI) and electron capture detection (ECD) [21, 22]. 2,3,4,5,6-Pentafluorobenzoyl chloride (PFBoylCl) has been shown to provide the sensitive detection of steroids [23-25], amines [26, 27], and endocrine disrupting compounds [28, 29]. PFBoyl-derivatization has shown the potential to sensitively detect the esters of PFBoyl-derivatized FOH in biological samples when employing selected ion monitoring (SIM) methods [30-32].…”

Section: Introductionmentioning

confidence: 99%

An examination of pentafluorobenzoyl derivatization strategies for the analysis of fatty alcohols using gas chromatography/electron capture negative ion chemical ionization–mass spectrometry

Bowden

Ford

2011

Journal of Chromatography B

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Gas chromatography/electron capture negative ion chemical ionization-mass spectrometry (GC/ ECNICI-MS) combined with pentafluorobenzoyl derivatization (PFBoyl) is frequently used for the sensitive detection of fatty alcohols (FOH). However, this derivatization technique suffers from a lack of established reaction protocols, time-consuming reactions, and the presence of reagent artifacts or unwanted derivatization byproducts which can hinder analyte detection. Here, strategies are presented to reduce the problems associated with PFBoyl-derivatization, including 1) the optimization of reaction conditions (derivatization time and temperature) for a variety of PFBoyl-derivatized FOH, 2) an investigation of microwave-accelerated derivatization (MAD) as a rapid alternative heating mechanism for the PFBoyl-derivatization of FOH, and 3) an analysis of an alternative strategy employing a solvent extraction procedure post-derivatization to reduce the detrimental effects commonly associated with PFBoyl derivatization reagents. The optimal reaction conditions for the PFBoyl-derivatization of FOH was determined to be 60 °C for 45 min. The investigation in MAD demonstrated the potential of obtaining comparable PFBoylderivatizations to those obtained using traditional heating methods, albeit in a reaction time of 3 min. An examination of several solvents for post-derivatization extraction revealed improved relative response factors in comparison to those obtained without solvent extraction. The best solvents for the PFBoyl-FOH extraction, dichloromethane and tert-butyl methyl ether, were also compared to the no solvent extraction samples with standard response curves and PFBoylderivatized FOH in Bligh-Dyer extracted rat plasma. KeywordsGas chromatography/mass spectrometry (GC/MS); fatty alcohols (FOH); pentafluorobenzoyl chloride (PFBoylCl); electron capture negative ion chemical ionization (ECNICI); postderivatization extraction

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An evaluation of the negative ion mass spectra of electron-capturing derivatives of the biogenic trace amines I—phenylethylamine

Durden¹

1991

Biol. Mass Spectrom.

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A series of fluorinated derivatives have been examined for their suitability of use for quantification of biogenic trace amiaes, in particular phenylethylamine, in biological samples at the picogram (femtomolar) level using aegotive ion ma= spectrometry. The negative ion mass spectra of the pentafluoropropionyl, heptafluorobutyryi, perfluorasuccinimido, pentafluorobemyl and pentafluorobemoyl derivatives of phenylethyhmine are characterized by intense high-mass fragment ion peaks due to loss of HF, whereas the spectra of the 3-trifluoromethylbemoyl, Qtrifluorometbylbenzoyl and 3,5-di-trifluoromethylben~yl derivatives exhibited fragment ions due to loss of H or 2H and the pentafluorobemoyl derivative did not form a detectable molecular ion. After acetylating the fluorobenzoyi derivatives of phenylethylamine, the spectra of the resultant amides were found to contain primarily molecular ions, and the electron capture cross-sections and negative ion sensitivities increased. The most suitable derivatives were fouud to be the N-acetyl-N-pentafluorobenzoyl, which could be detected at the 75 fg (0.5 attomolar) level of phenylethylamine and the N-acetyl-N-3,!5di-(trifluoromethy1)beayl derivative.

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Analysis of the pentafluorobenzoyl derivative of phenylethylamine utilizing negative ion chemical ionization and gas chromatography/mass spectrometry

Cited by 4 publications

References 6 publications

Electron-Capture Mass Spectrometry: A Powerful Tool in Biomedical Trace Level Analysis

Electron-Capture Mass Spectrometry: A Powerful Tool in Biomedical Trace Level Analysis

An examination of pentafluorobenzoyl derivatization strategies for the analysis of fatty alcohols using gas chromatography/electron capture negative ion chemical ionization–mass spectrometry

An evaluation of the negative ion mass spectra of electron-capturing derivatives of the biogenic trace amines I—phenylethylamine

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